There have been many attempts in rock'n'roll to distil the experience of heartbreak – not the wider misery exactly, the wailing and the wretchedness, but of a lover's ability, as the Decemberists once put it, "to rend your ventricles apart." Among my favourite musical dissections of the human heart is the final verse of Bob Dylan's You're a Big Girl Now, which appears on his 1975 album Blood on the Tracks – though my preferred version is the rawer, rougher demo, which appears on 1985's Biograph collection. It documents all the pain and confusion of a break-up before arriving at those last, wrenching lines: "I'm going out of my mind," he bleats, "With a pain that stops and starts/ Like a corkscrew to my heart/ Ever since we've been apart."

Though Dylan claimed in his autobiography, Chronicles Vol 1, that the songs on Blood on the Tracks were inspired by the stories of Chekhov, I'm not altogether sure we should believe him. It has long been supposed that he was writing about the breakdown of his own marriage to Sara Lownds, a belief bolstered by their son, Jakob, who once noted: "The songs are my parents talking." Even the album's title suggests the physical pain, the love spilled on its songs.

Paul Simon's 1986 album Graceland was also something of a break-up album, its title track mapping a journey made to Elvis Presley's former home in the wake of a separation: "Losing love," he sings, "is like a window in your heart/ Everybody sees you're blown apart/ Everybody feels the wind blow." Simon has been quite open about the inspiration behind this song – the grief and disorientation following the split from his second wife, Carrie Fisher.

Not so very long before, Fisher had been Simon's subject for Hearts and Bones, a song about "the arc of a love affair". "You take two bodies and you twirl them into one," Hearts and Bones ran. "Their hearts and their bones/ And they won't come undone." By the time of Graceland, though, Simon finds himself undone, and craving some kind of salvation. "It had to do with finding a metaphorical Graceland," he explained. "A state of grace, a state of acceptance."

There are echoes in Dylan and Simon's songs that extend beyond their thematic similarities. Both reference brief final conversations and words of wisdom from their former lovers. Dylan notes a last exchange that was "short and sweet", and later observes that "Love is so simple, to quote a phrase/ You've known it all the time, I'm learning it these days." Simon, meanwhile, speaks of his love coming back solely "to tell me she's gone". And it is she who first compares lost love to a window in your heart.

But there are distinct differences, too. While Simon hunts for that metaphorical state, Dylan is trying to make things more real, more physical: he talks of birds on fences, of time as a jet plane, changes in weather and horses midstream, transforming each example into a reference to the failed relationship. All seem to lead to the sharp, twisting pain of the corkscrew to the heart, as if this is love loss at its root.

In Simon's song, the heart is empty and windblown, and lies in a broader landscape. The tale of his divorce is carried between stories of the Mississippi river and the music of his youth, verses crammed with "poor boys and pilgrims" there alongside tales of love's absence; if Dylan gave us the keen something of heartbreak, then here Simon gives us the devastating nothingness. But after this nothingness comes a hope. As the song, and the album progress, Simon finds solace in music, following rock'n'roll back to its beginnings, to Graceland and to Africa. In so doing, he seems to rediscover his heart, still beating and full once more, its resilience drawing an easy parallel with music itself; both such rooted, rhythmic things. "This is the powerful pulsing of love in the vein," he exclaims on Under African Skies. "After the dream of falling and calling your name out/ These are the roots of rhythm/ And the roots of rhythm remain."

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